After 75 Years, the Headless Horseman of Sleepy Hollow Is Still One of the Spookiest Disney Villains
By the time I actually read Washington Irving’s short story “The Legend of Sleepy Hollow” for the first time in a college American Literature class, I had already been very well aware of the ghostly tale from Disney‘s animated presentation of it that was featured as part of the package film The Adventures of Ichabod and Mr. Toad.
That movie, produced by Walt Disney and distributed by RKO, had its premiere on Oct. 5, 1949, and included two segments. First was an adaptation of Kenneth Grahame’s children’s novel The Wind in the Willows (featuring characters like Mr. Toad), which was narrated by Basil Rathbone.
Second on the bill was an adaptation of Irving’s story about poor Ichabod Crane’s confrontation with the infamous Headless Horseman, which had narration (and three songs!) provided by Bing Crosby.
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I wasn’t aware until much later that Disney’s Sleepy Hollow had originally been paired with Willows in a single movie. I don’t know if I’ve ever even seen that latter film, though I have read Grahame’s novel and I enjoyed Mr. Toad’s Wild Ride, which was inspired by Willows, when I rode it at Disney World as a kid. (The ride apparently only still exists at Disneyland, one of that park’s few remaining original attractions from its 1955 opening.)
Maybe The Wind in the Willows did air at times during The Wonderful World of Disney, which I would tune in for on Sunday nights back in the day, and maybe I did see it there at some point.
But out of this double feature, the one I definitely did look forward to, especially around Halloween time, was The Legend of Sleepy Hollow. I don’t think it aired on Wonderful World of Disney every year, but I always tuned in to see if it would be part of the Halloween episode. When it was, I was excited and thrilled (and a bit scared) as I watched it.
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Seeing it again as an adult, I still am awed (and spooked at times) by Disney’s presentation of this story. From what I understand, both entries in this package film were originally planned as feature-length films. Willows might have worked in that format, given it came from a novel, but I’m glad they ended up keeping Sleepy Hollow on the short story side, which I think enhances its effectiveness.
The animation, of course, is simply gorgeous; colorful and flowing, with wonderful contrasts between lights and darks, especially during the climactic forest pursuit of Ichabod by the Horseman.
Like most Disney animated movies of the time, there is a song-and-dance element to this short film, with Crosby performing tunes associated with three primary characters: “Ichabod Crane,” “Katrina” and “The Headless Horseman.”
The latter song is the most entertaining. It’s performed at a Halloween gathering by Brom Bones, who is Ichabod’s rival for the affections of the lovely Katrina Van Tassel. Brom is certainly a jerk, but Ichabod is no prize, either, as we discover when we first meet him, so it’s kind of fun to watch Brom tease the superstitious and cowardly schoolmaster with this spooky (and catchy) song that introduces him (and us) to the spectral subject of Sleepy Hollow’s legend:
Right after getting freaked out by that little ditty, Ichabod remembers that he has to ride his horse home. Alone. At night. Through the forest reportedly haunted by the Horseman.
That gives the animators and sound designers of the film a chance to inject a wonderful combination of chills and laughs, as Ichabod (like all of us might in that situation) imagines ghosts and monsters behind every sight and sound, including imagining hearing his own name being called — “ICH-A-BOD” — which turns out to just be frogs croaking, or thinking he hears the thunderous clap of a horse’s hooves coming up behind him, which is just the wind knocking cattails upon a log.
Realizing the natural explanations behind what is scaring him, Ichabod and his trusty (and just as cowardly) horse end up laughing over it.
But soon, their merriment is joined by booming laughter coming from a nearby cemetery. That laughter isn’t jolly, but loud, echoing and sinister-sounding. Ichabod looks up to see the dreaded Horseman, astride his rearing mount, and holding a sword and a flaming jack-o-lantern. The chase is on.
The Horseman’s pursuit of Ichabod is still marvelous to look at, and it is where the animation of the film really shines. The sequence deftly moves from Looney Tunes-like humor as Ichabod and his horse collide with trees or get turned around just before they can safely cross the bridge (as the earlier song told Ichabod and us, “Once you cross that bridge, my friend, the ghost is through — his power ends”), to genuinely creepy scenes of the Horseman, who continues his evil laughter throughout the chase.
There is a moment where the Horseman and his mount leap high into the air, with heir shadowy forms and red cape silhouetted against the full moon, that is just breathtaking.
The Horseman’s steed is scary in its own right; at the outset of the chase, we see the dark head and demonic red eyes of the horse right on the heels of Ichabod and his mount, so close they can feel its hot breath panting onto them.
In some versions of “The Legend of Sleepy Hollow,” and even from what I recall of Irving’s story, while it isn’t overtly stated, it can be inferred that it was Brom Bones in disguise as the Horseman who actually pursued Ichabod, hoping to drive him away from Sleepy Hollow (and from Katrina).
Remind But in Disney’s take on the tale, I can actually believe the Horseman is a ghost. At one point, Ichabod and the Horseman collide, and Ichabod has a chance to look down the cloak of his pursuer, into the neck area where a head should be. If it were Brom, he likely would have been seen, even hidden down in the cloak a bit. But all that comes out of that cloak is more of the Horseman’s laughter, echoing hollowly throughout the woods.
(I have to say, whoever provided the laughter for the Horseman gave us one of the most terrific sinister laughs in screen history.)
Just as I did as a kid, I try to watch Disney’s take on “The Legend of Sleepy Hollow” around Halloween each year. It’s easier now that it is available on the internet, and I don’t have to eagerly await the Halloween edition of The Wonderful World of Disney and hope it will be included. But that was still a fun time, and watching it again now gives me a little nostalgic thrill in addition to the chills of the story itself.
This film clearly has resonated in similar ways with others, including Tim Burton, who made nice reference to it in his fun 1999 feature Sleepy Hollow.
While the actual Horseman in Burton’s movie ultimately does have a supernatural origin, there is a scene where it is indeed Brom (Casper Van Dien) dressed as the Horseman who frightens Ichabod (Johnny Depp) as he is crossing a bridge. We get references from the Disney feature like the frogs seeming to croak “ICH-A-BOD” and even the Horseman tossing a pumpkin across the bridge at Ichabod.